Synthesis, characterization, and crystal structure of 1-(4-chloro-benzoyl)-3-naphthalen-1-yl-thiourea

1-(4-Chloro-benzoyl)-3-naphthalen-1-yl-thiourea has been synthesized and characterized by elemental analysis, IR spectroscopy, and mass spectrometry. The crystal and molecular structure of the title compound has been determined from single crystal X-ray diffraction data. It crystallizes in the triclinic space group P-1, with a = 6.962(1) Å, b = 10.770(3) Å, c = 11.738(2) Å, = 65.76(2)°, = 80.03(1)°, = 84.86(2)°, and D _calc= 1.432 g cm^–1 for Z = 2. The thermal behavior of the compound has been studied by DTA and TG. The antibacterial activities of the title compound were investigated for three Gram (+) and two Gram (–) bacteria by employing broth microdilution method and subsequently, inhibitory activity against yeast-like fungi was also determined.     

Synthesis and structure of 4-R,5-R-[5-(hydroxy-diphenyl-methyl)-2, 2-dimethyl-[1,3]dioxolan-4-yl]-phenyl-methanone, a chiral ligand building block

A triphenyl analog of taddol, 4-R,5-R-[5-(hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-phenyl-methanone, has been synthesized and structurally characterized. This molecule could act as a chiral ligand building block in the creation of tuned taddol analogs. Structural analysis of the title compound reveals that the hydroxyl group is involved in an intramolecular hydrogen bond and does not take part in any intermolecular interaction. Crystal packing is influenced by C–H O hydrogen bonding and phenyl phenyl interactions. Crystal data: Triclinic, P1 (No. 1), a = 5.9343(4) Å, b = 8.2367(17) Å, c = 10.987(2) Å, = 88.290(6), = 75.442(4), = 80.655(6), V = 512.86(15) ų, Z = 1, D _calc = 1.258 mg/m³. Final residual values were R ₁ = 0.0407 for 3022 observed data (I > 2s(I) ) and wR ₂ = 0.0941 for all 3524 unique data.     

X-ray diffraction structure of (5S)-3,4-dichloro-5-menthoxy-2(5H)-furanone

The structure of (5S)-3,4-dichloro-5-menthoxy-2(5H)-furanone is reported. The title compound crystallizes in the monoclinic space group P2₁: a = 6.650(2) Å, b = 8.038(3) Å, c = 14.858(8) Å, = 97.01(3), V = 788.3(6) ų, Z = 2, R = 0.0718, R _w = 0.0795 for 735 observed reflections with I > 3 (I), and the absolute configuration at C-5 of the furanone ring is shown to be (S).     

Solid-state conformational heterogeneity of the 2,2,5,5-tetramethyl-3,4-hexandione monohydrazone: X-ray diffraction and MAS NMR experiments

The X-ray diffraction study of the 2,2,5,5-tetramethyl-3,4-hexandione mono-hydrazone 1 shows a solid solution of two screwed conformers in the crystal. In each of these conformers, the conjugated C=O and C=N double bonds have an approximately perpendicular orientation with = 101.1°(2) and –93.4°(2), respectively. AM1 theoretical calculations give the same result for the isolated molecule. The calculated rotational barrier around the central single bond of the conjugated moiety is about 45.98 kJ mol^–1 which is higher than the classical values observed for 1,3 conjugated systems (28.42 kJ mol^–1 in the 1,3-butadiene). Variable temperature ¹³C CPMAS NMR experiments show hindered rotation around the COC(CH₃)₃ tert-butyl group in the solid state. 1 crystallizes in the triclinic space group P ₁ with a = 10.106(1)Å, b = 11.698(1)Å, c = 12.313(1)Å, = 62.108(1)° = 70.517(1)° = 66.052(1), V = 1157.0(3)ų, D _calc = 1.06 with Z = 4.     

Structural studies of N(4)-substituted thiosemicarbazones prepared from 4-formylantipyrine and a thiourea derived from 4-aminoantipyrine

Reaction of 4-formylantipyrine with N(4)-dimethylthiosemicarbazide and 3-piperidylthiosemicarbazide produces the N(4)-dimethylthiosemicarbazone (1), and the 3-piperidyl-thiosemicarbazone (2), respectively. Compound 1 is triclinic, space group P-1 with a = 6.329(1) Å, b = 11.699(1) Å, c = 11.943(1) Å, = 65.83(1)°, = 80.83(1)°, = 84.90(1)°, and V = 796.1(1) ų with Z = 2, for D _calc = 1.324 g/cm³. Compound 2 is triclinic, space group P-1 with a = 6.784(1) Å, b = 10.485(2) Å, c = 13.462(3) Å, = 102.05(2)°, = 98.61(2)°, = 101.32(2)°, and V = 899.8(5) ų with Z = 2, for D _calc = 1.319 g/cm³. Reaction of 4-aminoantipyrine with phenyl isothiocyanate produced N-antipyrine-N-phenylthiourea (3). Compound 3 is monoclinic, space group P2₁/n with a = 6.863(7) Å, b = 15.361(3) Å, c = 16.332(5) Å, = 90.35(6)°, and V = 1720.7(18) ų with Z = 4, for D _calc = 1.306 g/cm³. Compounds 1 and 2 have intermolecular hydrogen bonding between the carbonyl oxygen of the antipyrine moiety and the NH hydrogen of the thiosemicarbazone moiety. In 3 the two unique molecules are held together as a dimer by interactions of the two thiourea NH's and the antipyrine moiety's\break oxygen.     

Crystal structure of benzimidazolium dichromate

The X-ray crystal structure of benzimidazolium dichromate is determined. The compound C₁₄H₁₄Cr₂N₄O₇ is Triclinic in P-1 with a = 8.2722(8) Å, b = 10.0269(10) Å, c = 11.7001(11) Å, = 102.073(2)°, =100.483(2)°, = 67.288(2)°, V = 869.88(15) ų, D _calc = 1.734 g/cm³, and Z = 2. A dichromate ion connects two benzimidazolium rings via hydrgen bonds, as leads to face-to-face intramolecular aromatic stacking. The major force of crystal formation comes from hydrogen bonds, and an intermolecular hydrogen bridge is formed to connect two neighbored dichromate ions.     

Crystal structure of γ-2-trans-2,6-diphenylthian-1,1-dioxide-4-one oxime, C17H17NO3S

The X-ray crystal structure of -2-trans-2,6-diphenylthian-1,1-dioxide-4-one oxime is determined [C₁₇H₁₇NO₃S, space group P2₁ n, a = 8.177(1) b = 9.574(1)c = 19.730(5) Å, = 97.35(5)°]. The oxime group does not form an oxime dimer, but is involved in an O-H···O=S hydrogen bond.     

Structure of 2-{2-[3-methyl-3-(2,4,6-trimethylphenyl) cyclobutyl]-2-oxoethyl}isoindole-1,3-dione

2-{2-[3-Methyl-3-(2,4,6-trimethylphenyl)cyclobutyl]-2-oxoethyl}isoindole-1,3-dione (C₂₄ H₂₅NO₃) was synthesized, and its crystal structure was determined by X-ray crystallographic techniques. The compound crystallizes in the triclinic space group P-1, with unit cell parameters: a = 14.109(9) Å, b = 14.130(8) Å, c = 12.152(6) Å, = 105.62(5)°, = 113.75(4)°, = 98.78(5)°, V = 2039.8(19) ų, D _c= 1.223 g/cm³, and Z = 4. The crystal structure has two crystallographically independent molecules, I and II. These molecules are held together by weak intermolecular C—H···O interactions, forming a continuous chain. The dihedral angles between the N-substituted phthalimide moiety and cyclobutane ring in molecules I and II are 60.37(14) and 68.18(18)°, respectively.     

Crystal structure and spectroscopic study of 4-(N-acetyl) cysteinyl-6,7-dimethoxy-2,2-dimethyl-3-hydroxybenzo-1H-pyran,a potential metabolite of glutathione conjugation of precocene II 3,4-epoxide

The X-ray crystal structure of the title compound has been determined. The crystals are monoclinic:P2₁/a, a=9.804(7),b=20.544(4),c=13.288(3) Å,=105.94(4)°,V _c=2561.9 ų,Z=4,D _x=1.39Mg m^–3, (MoK)=0.71069 Å. The structure was solved by direct methods and refined with 2147 reflections to a finalR value of 0.072. The 1h-pyran ring departs from ideal symmetry towards a half-chair conformation. Mass, IR, and¹H NMR spectra are also reported.     

4- and 5-nitroindane

Mononitration of indane produces a mixture of 4- and 5- nitroindanes. Crystallization from mixtures occurs after distillation improves composition of a major component to above 80%. 4-Nitroindane: triclinic, space group (#2),a=7.332(4) Å,b=8.304(4) Å,c=8.358(4) Å, =61.43(4)°, =67.60(4)°, =70.15(4)°,V=405.4(4) ų,Z=2. Non-H-atoms are nearly planar, aliphatic H's are eclipsed. 5-Nitroindane: monoclinic, space groupP2₁/c (#14),a=10.946(8) Å,b=15.643(10) Å,c=9.415(6) Å, =92.34(5)°,V=1611(2) ų,Z=8. Non-H-atoms in the two molecules differ in torsion of the nitro group with respect to indane and fold of the nonbenzylic methylene group. Semiempirical calculations (PM3) suggest that distorsion from planarity may be associated with the two lowest energy vibrational modes. Uv, ir, ms, proton, and¹³C-nmr spectra are correlated with the solid state structures.     

New polydentate sulfide ligands: Synthesis, redox properties, and molecular structure of 4,5-bis(p-tolylthio)-4-cyclopenten-1,3-dione

The reaction of p-toluenethiol with 4,5-dichloro-4-cyclopenten-1,3-dione in 1,2-dichloroethane with added DBU affords good yields of the new bidentate sulfide ligand 4,5-bis(p-tolylthio)-4-cyclopenten-1,3-dione. The title compound was isolated by column chromatography and characterized in solution by IR and NMR spectroscopies. The solid-state structure of RC=CRC(O)CH₂C(O) (where R = p-tolylthio) was solved by X-ray crystallography. 4,5-Bis(p-tolylthio)-4-cyclopenten-1,3-dione crystallizes in the monoclinic space group P2 ₁/c, a = 14.203(3) Å, b = 6.181(1) Å, c = 20.372(4) Å, = 106.111(3)°, V = 1718.1(6) ų, Z = 4, and d _calc = 1.316 mg/m³; R = 0.0743, R _w = 0.1693 for 3958 reflections with I > 2(I). The redox properties of 4,5-bis(p-tolylthio)-4-cyclopenten-1,3-dione have been examined by cyclic voltammetry in CH₂Cl₂ solution, where a quasireversible reduction wave at –1.10 V was found. The reduction behavior is discussed relative to the nature of the LUMO level, which has been determined by extended Hückel MO calculations. The redox chemistry and the LUMO of our bidentate sulfide ligand are contrasted with the known redox chemistry and the LUMO composition of the corresponding bidentate phosphine ligand 4,5-bis(diphenylphosphino)-4-cyclopenten-1,3-dione (bpcd).     

Crystal structure of pyrazole derivatives. IV. 5-chloro-4-chlorosulfonyl-3-methyl-1-phenylpyrazole

The title compound crystallizes in space groupP2 ₁/a witha=17.063(1),b=13.208(1),c=21.260(2) Å, =99.51(1)°,V=4726(1) ų,Z=16, there are four independent molecules in the asymmetric unit. The phenyl and pyrazole rings are planar, to within experimental accuracy, making different dihedral angles in the independent molecules: 42.2(1), 129.5(1), 52.5(1), and 46.2(1)°.     

4- and 5-nitro-2-benzoylbenzoic acid

The structures of two isomeric nitro 2-benzoylbenzoic acids have been determined. 4-Nitro-2-benzoylbenzoic acid, C₁₄H₉NO₅, monoclinic, P2₁/c, a = 9.455(5), b = 6.632(2), c = 21.333(7)Å, = 107.96(3)°, Z = 4, V = 1270.6(9)ų, 5-nitro-2-benzoylbenzoic acid, C₁₄H₉NO₅, monoclinic, P2₁/c, a = 10.201(6), b = 8.515(4), c = 14.573(7)Å, = 101.35(4)°, Z = 4, V = 1241.1(11)ų. Both carboxylic acids form the usual H-bonded dimers across crystallographic centers of inversion. The nitro groups are essentially in the ring planes, and the interplanar angle between the mean planes described by the atoms of the benzoyl substituents and those of the benzoic acid aryl rings are 69(1)° and 84(1)°, respectively. The lower cell volume, higher density, and lower solubility in ethyl ethanoate correlates with the greater packing efficiency in 5-nitro-2-benzoylbenzoic acid.     

Synthesis and crystal structure of 4-(p-methoxyphenyl)-3, 5-bis(4-pyridyl)-1,2,4-triazole

The 4-(p-methoxyphenyl)-3,5-bis(4-pyridyl)-1,2,4-triazole has been synthesized and its crystal structure has been determined by X-ray diffraction methods. It crystallizes in the monoclinic space group P2₁/n, with a = 12.5832(6) Å, b = 7.0512(5) Å, c = 18.4669(12) Å, = 96.826(1)°, and D_calc = 1.345 g cm^–1 for Z = 4. In the structure, two pyridyl rings, phenyl ring, and triazole ring do not share a common plane. The most favored orientation of the pyridyl rings in the crystal is that their planes are inclined toward opposite directions with respect to the triazole ring.     

Structure of 4-(2-chloro-4,5-dimethoxybenzylidene)-2-methyl-5-oxazolone. X-ray and NMR study

The azlactone of 6-chloroveratraldehyde 3 (4-(2-chloro-4,5-dimethoxybenzylidene)-2-methyl-5-oxazolone) was synthesized from 6-chloroveratraldehyde 2 and its structure investigated using X-ray crystallographic and nuclear magnetic resonance methods. Compound 3 crystallized in the P2₁/c (#14) space group (Z = 4) with cell dimensions a = 9.148(2), b = 22.938(2), c = 6.707(1) Å, and = 111.50(2)°. The X-ray study shows that azlactone 3 exists as the Z-isomer and crystallizes as a planar structure, i.e., both the phenyl and azlactone ring systems, as well as the functional groups attached to them, lie in the same plane. The ¹H and ¹³C NMR spectral values also support the formation of the Z-isomer only, during the synthesis of 4-(2-chloro-4,5-dimethoxybenzylidene)-2-methyl-5-oxazolone.     

Nonpreorganized neutral acyclic anion receptors: Structural investigations of N,N′-diphenyl-1, 3-benzenedisulfonamide and N,N′bis(4-t-butylphenyl)-1, 3-benzenedisulfonamide

The structure of N,N-diphenyl-1,3-benzenedisulfonamide (1) was determined by single crystal X-ray diffraction. It crystallizes in P2₁/n with cell dimensions: a = 11.8390(6) Å, b = 12.3950(10) Å, c = 12.1184(10) Å, = 94.388(6)°, and V = 1773.1(2) ų. Its di-t-butyl derivative, N,N-bis(4-t-butylphenyl)-1,3-benzenedisulfonamide (2), was prepared and structurally characterized as two solvated structures. Both crystallize in P with cell dimensions: 2 CF₃CH₂OH, a = 9.469(2) Å, b = 10.0039(18) Å, c = 16.385(3) Å, = 85.561(16)°, = 83.035(18)°, = 72.459(16), and V = 1467.7(5) ų; 2 ClCH₂CH₂Cl, a = 9.559(2) Å, b = 9.8125(12) Å, c = 17.100(6) Å, = 82.495(19)°, = 83.47(2)°, = 70.100(15), and V = 1491.1(6) ų. The structures exhibit hydrogen-bonding, and are evaluated in terms of preorganization for anion binding.     

Preparation and crystal structure of tungstogallate acid H5GaW12O40

The heteropoly tungstogallate acid H₅GaW₁₂O₄₀ has been synthesized and characterized. Colorless octahedral crystals of the title compound were crystallized from acetonitrile with formula H₅GaW₁₂O₄₀. The single crystal X-ray structure analysis of the title compound revealed that it crystallized in monoclinic system, space group Cm with a = 17.691 (4) Å, b = 25.065 (5) Å, c = 15.315 (3) Å, = 125.21 (3)°, V= 5548.5 (19) ų, and Z = 2. The crystal consists of the heteropolyanion GaW₁₂O ₄₀ ^5– and H⁺ cations. The heteropolyanion GaW₁₂O ₄₀ ^5– is an independent unit and assumed to have the Keggin structure.     

Crystal and molecular structure of 2,2-diphenyl-5-dichloromethylene-3-oxazoline-4-ethylcarboxylate

The structure of an oxazoline compound: 2,2-diphenyl-5-dichloromethylene-3-oxazoline-4-ethylcarboxylate has been established uniquely by X-ray crystallography. C₁₉H₁₅Cl₂NO₃ is monoclinic, space groupP2₁/n, with the cell dimensionsa=8.170(1),b=23.559(2),c=9.962(1) Å,=105.53(1)°,V=1847.5(3) ų,Z=4,M _r=376.2,D _x=1.35,D _o=1.36 g cm^–3,F(000)=776,T=293 K,=33.2 cm^–1, finalR=0.062 for 2321 observed reflections. Two phenyl rings make a dihedral angle of 83.3(4)° and are equally inclined to oxazoline ring plane. The ethylcarboxylate group is planar and is at an angle of 76.1(4)° with respect to oxazoline ring plane.N.C.L. Communication No. 5360.     

Structure of dichloro[(2,4-dimethyl-5-oxo-2,3,4,5-tetrahydro-2-furyl)methyl]-(4-methoxyphenyl)tellurium(IV)

The crystal structure of TeCl₂(C₇H₇O)(C₇H₁₁O₂) has been determined from three dimensional, single crystal X-ray diffraction data. It crystallizes in the monoclinic space group C2/c with the lattice constantsa=24.551(5),b=11.435(2),c=12.368(2)Å,=97.33(1)° andZ=8,D _X=1.67 g cm^–3. Final least-squares refinement based on 3023 independent observed reflections yieldedR=0.026. The Te^iv ion is in a trigonal bipyramidal configuration with its lone pair of electrons at one of the equatorial positions. Distances and angles are: Te-Cl=2.495(1), 2.517(1); Te-C=2.134(3), 2.106(3)(aryl)Å; Cl-Te-Cl=173.45(4), Cl-Te-C=88.11(9), 88.60(9), 88.72(9), 86.06(9); C-Te-C=96.5(1)°. There are two secondary bonds to the tellurium: TeCl=3.824(1) and TeO(2)=3.006(1)Å. The methyl group to the carbonyl oxygen and the aryltelluro moiety exhibit atrans 2,4 relationship.     

Spectroscopic and crystal structure analyses of methyl 1-phenyl-3,4-dioxo-2-naphthalenecarboxylate,C18H12O4

The crystal and molecular structure of methyl 1-phenyl-3,4-dioxo-2-naphthalenecarboxylate, C₁₈H₁₂O₄, has been determined from three-dimensional, single-crystal X-ray diffraction data. The compound crystallizes in the monoclinic space groupCc(No. 9, C _s ⁴ ) witha=9.837(2),b=16.397(3),c=8.706(1) Å,=94.88(1)°,Z=4,D _m =1.38(1) Mg m^–3, andD _x =1.388 Mg m^–3. The phasing model was determined by direct methods and the final full-matrix least-squares refinement yieldedR=0.0363 and R_w=0.0405 for 1374 unique reflections. Optical, infrared, NMR, and UV-VIS analyses have also been carried out. The molecules in the crystal lattice are held together by van der Waals forces.3-Carbomethoxy-4-phenyl-1,2-naphthoquinone.